💛 That “Quick Check-In” Might Be Hurting Your Team

Hello and happy Thursday!

I have a confession to make.

In my early years as a people manager, one of worst habits was canceling 1:1 meetings with my team. I was notorious for it.

At the time, I told myself it was fine. I didn’t have anything urgent to talk about, my calendar was jam-packed, and other meetings felt more pressing. But looking back, I realize I was slowly chipping away at something much more important: trust, consistency, and connection. Not to mention, all my “reasons” for rescheduling fully centered me - when those meetings were really for and about my team.

It wasn’t until a courageous team member called me out that I began to understand the impact. More importantly, I started asking myself why these meetings mattered in the first place.

What I wish someone had told me then is that not all team meetings are created equal - and knowing the difference between them changes everything. Once you understand the purpose behind check-ins and 1:1s, it becomes much easier to use both effectively, and much harder to skip them altogether.

While building our Training for the Modern Manager curriculum, I spent a lot of time learning about manager meeting best practices. And here’s the thing: there isn’t one perfect format. What matters is building a structure that fits your team’s culture, setting clear expectations around that structure and then holding managers accountable (::cough:: rewarding them prioritizing it ::cough::) to sticking to it.

Today, I want to walk you through the two meetings that shape the foundation of great manager-employee relationships: the check-in and the 1:1. While they may seem interchangeable at first glance, each plays a distinct role—and getting them right can make a big difference in how your team feels and performs.

Yours in learning from mistakes,

Jill

It’s not a stretch to claim that most managers are thrown into their role with little to no support or training on what being a great manager actually looks like. It’s literally why I built a management training curriculum with the explicit goal of making this support accessible to more organizations.

Given this knowledge gap, can we really blame them for not understanding the true importance of regular employee meetings?

No, we can’t.

Which is why we’re dedicating this week’s newsletter to showcasing some best practices that can easily be introduced to and executed by your managers, regardless of whether they are remote, hybrid or fully in-person.

A check-in is a meeting designed to focus on the work itself.

These conversations give managers a consistent opportunity to understand how projects are progressing, identify blockers early, and offer support before small issues turn into larger ones.

Where check-ins tend to go sideways is when they veer into conversations that are better suited for 1:1s - like performance feedback, employee satisfaction, or personal challenges. We’ve all had one of those “can we do a quick check-in?” messages that turned out to be something much deeper (and more stressful) than we were expecting.

Keep the conversation focused on work. Check-ins should revolve around current projects, progress toward goals, and any obstacles the employee is facing. If personal issues or broader concerns arise, acknowledge them, but save the deeper conversation for your next 1:1 (more on this below!).

Be flexible with the format. These touch-points can be either synchronous (live meeting) or asynchronous (shared written updates), depending on the team and culture. While many teams meet live, others use tools like Lattice, 15Five, Slack, or Google Docs to collect written updates. The key is consistency, not the format.

Cadence can vary, but weekly is standard. For most teams, weekly check-ins strike the right balance. While more senior team members may not need them as often, the key is maintaining regular visibility into how work is progressing.

Your response is important! During live check-in meetings, managers must be focused on active listening, not multitasking. Those utilizing written async check-ins must prioritize reading and responding to employee submissions within 48 hours or else they quickly become a wasted activity (like those employee engagement results that never result in action). Taking a few minutes to comment on their responses and leave a thoughtful question or two will go a long way!

Foster psychological safety. Employees will only be as candid as they feel safe to be. The way you respond to early signs of struggle sets the tone for future honesty and transparency.

Coach your team on what a good check-in looks like. Help team members develop updates that are specific, honest, and useful. Share examples, offer gentle feedback, and adjust the structure as needed.

Keep the structure consistent. Here’s a simple check-in structure we use and love:

1. What are your wins from last week?

2. What are you focused on for the upcoming week?

3. Are you facing any barriers or challenges?

4. How can I help you?

While check-ins are about the work, 1:1s are about the person and their overall experience at work.

The spotlight should be on the individual, not a project or task list. A well-run 1:1 creates space for meaningful conversation around topics like career growth, motivation, engagement, and overall well-being. The emphasis is on consistency, presence, and making space for meaningful, person-focused conversation.

In a remote or hybrid work environment, they’re also one of the most reliable ways to maintain connection and build trust.

When done well, 1:1s can serve as the glue that holds your manager-employee relationship together. When skipped or rushed, they can leave employees feeling invisible or unsupported, even if everything else on the team is running smoothly.

Keep focus on the person, not the work. While it might feel tempting to bring up project updates, those belong in a check-in. Use this time to talk about what motivates your employee, how they’re feeling about their role, and where they want to grow.

Being present is more important than being perfect. Your attention matters more than your agenda. Turn off notifications, close extra tabs, and show up ready to listen without distraction.

Let curiosity lead the way. You don’t have to have all the answers. Great 1:1s are built on open-ended questions and honest conversation. If your team member brings something up that you don’t know how to address, follow up afterward instead of guessing in the moment.

Cadence should be every other week, in real time. We recommend scheduling 1:1s every other week. Whether you’re in person or remote, these meetings work best when you can read body language and create space for non-verbal cues.

Come prepared. Bring questions that guide the conversation toward growth and connection. If your report doesn’t bring an agenda, your preparation can make the time meaningful. Lattice and Culture Amp both have great lists of suggested questions organized into categories like Employee Engagement and Morale and Career Aspirations.

Is distributed work actually working? Shelby Wolpa just released the 2025 Distributed Work Report which includes insights from 236 organizations! You’ll find high-level recaps of her top five takeaways here, where you can also download the executive summary (free) or purchase the full report ($99).

No - DEI is NOT illegal. There is no question that DEI work is under attack. That is why this reminder and explainer from Jennifer Laurie was the best thing I (Jill) saw on LinkedIn this week. The post is worth clicking, but in a nutshell:

“A new document from former EEOC leaders just dropped, and it says what many of us have already known: 1) You can still do DEI work. 2) You can still embed equity into your systems. 3) And no, it’s not all illegal.”

White Lotus Season 3 Finale (No spoilers unless you click through!): We can’t stop reading everyone’s wildly different opinions about the monologue Laurie (played by Carrie Coon) gives in the recent season finale of The White Lotus. You can read her full speech here and decide for yourself if it was a beautiful testament to the strength and longevity of female friendships, or a cop-out since it was painfully obvious the women had outgrown each other.